Few emotions linger as quietly, or as persistently, as regret. A smell, a scene in a movie, or a phrase someone says can remind us of regrets we’ve been carrying with us that linger in the background of our minds and hearts, perhaps for years.

Regrets can come from things we did, and perhaps even more difficult, from things we didn’t do.

• A relationship we didn’t pursue
• Words we never said
• An opportunity we passed by
• A career path not taken
• A mistake we wish we could undo
• Someone we didn’t spend enough time with

Many of us carry these moments for years, replaying conversations, imagining different choices, and wondering who we might have become if only we’d chosen another path, but regret doesn’t have to become a life sentence.

When we understand why we experience regret, and learn how to relate to it differently, it can become one of life’s greatest teachers instead of one of its harshest judges.

Why Did Regret Evolve?

If regret feels painful, it’s because it serves a purpose. Our brains evolved to compare what happened with what could have happened. This ability helps us learn from mistakes and make better decisions in the future. It can be very useful.

Without regret, we’d repeat harmful behaviors. In healthy amounts, regret reminds us that our choices matter. It reflects our capacity to imagine a better future.

The problem begins when learning turns into endless self-punishment. Instead of asking, What can I learn?, we begin asking, What’s wrong with me? Sometimes, we can get stuck in replaying the scenarios and paths not taken trying to solve the problem in an endless thinking loop. Stoic philosopher, Epictetus said in The Enchiridon,

“It’s not things themselves that disturb us, but our judgments about them.”

Healthy Regret Versus Rumination

Healthy regret is relatively brief depending on circumstances. It acknowledges what happened, extracts wisdom, and then allows us to move forward. Working through it feels complex, and it is, but it is nonetheless, it’s a process that we can move through like an arrow that travels forward.

Rumination is the opposite. It is a loop that keeps us circling regret infinitely. It continually reopens the wound without allowing it to heal.

• We replay conversations to figure out what people really meant or what we could have said or if what if we didn’t say something
• Recreate arguments in our minds to make that perfect point we should have said that might have shifted the whole situation and everything that happened afterwards
• Imagine alternate timelines of what if took another path, what if we did something else instead and where that might have led, or conversely if we hadn’t gone in a certain direction

In any case, when we ruminate we punish ourselves again and again with our own thoughts. Imaginary outcomes that never happened. At some point retrospection stops providing insight and becomes rumination. In other words, we’ve learned just about all we can and at this point thinking about it more becomes an unproductive doomloop that feels inescapable. In Letters From a Stoic, Seneca said,

“We suffer more often in imagination than in reality.”

Rumination is one of the most misunderstood psychological habits because it often feels productive. We tell ourselves we’re trying to understand what happened or prevent future mistakes. In reality, rumination often keeps us emotionally stuck without producing new insight.

So why do we do it? How can we tell when we’re moving from insight to rumination? It can be hard to discern this, but knowing some of the reasons why we ruminate might help you see it more clearly.

• We Believe More Thinking Will Produce a Better Answer. The brain evolved to solve problems. When something painful happens, especially something that feels unfinished, it assumes there must be an answer if it just thinks long enough. This works well for practical problems. It works poorly for irreversible ones. Many regrets have no additional information to uncover and no way to completely fix or reverse the outcome. At some point, thinking stops being problem solving and becomes emotional replay.
• We Are Trying to Regain Control. Regret reminds us that life is uncertain. By mentally replaying events, we create the illusion that we’re still influencing them. Psychologists sometimes describe this as an illusion of control. We revisit the past because it feels safer than accepting that some things cannot be changed.
• We Think Self-Punishment Is Responsible. Many people unconsciously believe that if they stop feeling guilty, they’ll become careless people or they’ll forget the lesson. So they keep punishing themselves. It’s as though suffering becomes payment for the mistake. But guilt has diminishing returns. After it teaches us what we needed to learn, continued punishment rarely produces additional wisdom.
• We Haven’t Fully Grieved. Sometimes regret isn’t really about the decision. It’s about mourning what never happened: a relationship, career, the child we never had, the city we never moved to. Rumination can become a way of refusing to let that imagined future disappear. We can live in that imagined world.
• Our Identity Is Threatened. We all carry stories about who we are such as being a good parent, competent, honest, careful. When we make a significant mistake, it doesn’t merely affect the event. It challenges the story we’ve been telling ourselves. Rumination often continues until we can build a new identity that includes both our strengths and our imperfections.

While this all may sound wild, remember our brains are trying to protect us from emotional pain.

• “If I replay this enough times…”
• “I’ll never make that mistake again.”

Unfortunately, the brain sometimes has trouble distinguishing between useful rehearsal and endless rehearsal. At some point, it’s practicing pain instead of wisdom.

When Mistakes Become Part of Our Identity

Psychologist Edith Eger, who survived the Holocaust, reminds us in her 2017 book The Choice: Embrace the Possible, 

“There’s a difference between guilt and shame. Guilt says, ‘I made a mistake.’ Shame says, ‘I am a mistake.'”

This distinction matters because healthy regret recognizes that we made a painful choice likely under impossible circumstances with limited information. We did the best we could.

Rumination convinces us that we are fundamentally flawed so many people stop seeing regret as something they experienced and instead, it becomes who they believe they are.

• “I’m the one who failed.”
• “I’m the one who ruined everything.”
• “I’m the one who missed my chance.”

Carl Jung believed that healing requires us to confront, rather than deny, the difficult parts of ourselves. We experience undesirable outcomes because we can’t control everything and sometimes we just make mistakes. In any case, we can move forward with insight and ground ourselves in reality by facing these truths. Carl Jung said in a lecture that,

“One does not become enlightened by imagining figures of light, but by making the darkness conscious.”

Our mistakes don’t disappear by pretending they never happened, nor do they define our entire identity. They simply become one chapter in a much larger story.

Forgive Your Younger Self

One reason regret hurts so much is that we judge our past selves using the wisdom we’ve gained since then. Our younger self didn’t possess today’s experience and they didn’t know what we know now. They acted with the understanding, emotional maturity, fears, and circumstances they had at the time. Roman emperor and Stoic philosopher, Marcus Aurelius said in Meditations, Book 12

“You have power over your mind, not outside events. Realize this, and you will find strength.”

If a close friend made the same mistake twenty years ago, would you condemn them forever? Probably not. So why offer yourself less compassion than you’d offer someone you love? Be a close friend to yourself.

There’s an important difference between remembering and reliving a doomloop. Remembering helps us understand whereas reliving keeps us emotionally trapped in the past. 

Making Peace With the Roads Not Taken

Some regrets aren’t about mistakes. They’re about possibilities.

• The career we didn’t pursue
• The city we never moved to
• The relationship that might have been

It’s tempting to imagine that the road not taken would have led to a perfect life, but we rarely imagine those alternate paths would likely have their own hardships and limitations. Remember,

• Every decision opens certain doors while quietly closing others
• No one gets to live every possible version of their life
• Accepting this reality can be painful, but it’s also freeing

Acceptance Is Not Approval

Many people fear that letting go of regret means saying what happened was okay. It doesn’t. Approval is saying something was good. Acceptance simply means acknowledging reality and saying it happened. There’s an enormous difference and Viktor Frankl may have said it well in his 1946 Holocaust memoir, Man’s Search for Meaning,

“When we are no longer able to change a situation, we are challenged to change ourselves.”

We may never approve of everything that’s happened, but we can stop fighting the fact that it happened. That’s how we can change ourselves.

Build Meaning (And Maybe a Future) From Your Mistakes

Some of the wisest people you’ll ever meet carry deep regrets. The difference is that they didn’t allow regret to be the final chapter. Instead, it became the beginning of greater compassion, humility, patience, and courage.

Frankl believed that human beings can find meaning even in suffering. Perhaps regret can become one of those places where meaning quietly grows.

Maybe your mistakes have made you kinder, more understanding, forgiving, or even more willing to help someone else avoid the pain you’ve known. That doesn’t erase what happened, but it changes what your suffering produces.

Closing Thoughts

Rumination promises understanding, but often delivers only familiarity. We replay the same memories so often that they become well-worn paths through our minds, yet familiarity isn’t the same as wisdom. Wisdom usually arrives when we’re willing to stop reliving the past long enough to begin living the present.

Returning to the present is the essence of mindfulness. When you find yourself doomlooping in regret, breathe, and use your senses. In the place you’re at, look at something, listen to something, smell something, feel something with your hand or on your skin. Maybe even taste something. As Sharon Salzberg wrote in Real Happiness, 

“Mindfulness isn’t difficult. We just need to remember to do it.”

None of us lives a perfect life. Every person carries memories of things they’d change if they could. The goal with regret isn’t to erase it as much as it is to transform it.

• Wisdom instead of punishment
• Remembering without reliving
• Forgiving without forgetting
• Accepting what can’t be changed while continuing to become someone new

Perhaps the greatest gift we can offer our past selves isn’t endless criticism, but gratitude. They survived long enough to become the person reading these words today. And this person, today, in this moment, is moving toward releasing regret, living in the present, and building their next chapter.

Reflection Questions

• What would I tell someone else who made my mistake?
• Am I punishing myself, or learning from what happened?
• What wisdom only exists because this happened?
• Is there a younger version of myself who deserves compassion instead of criticism?
• What would it look like to remember this experience without reliving it?
• How has this regret changed the way I treat other people?
• What meaning can I build from this chapter of my life?
• If I couldn’t change the past, how would I choose to live today?

Further Reading

Want to learn more about overthinking, self-awareness, emotional regulation, and taking meaningful action? Explore these articles and discover new perspectives.

• Can You Love Someone and Still Know They Are Wrong for You?
• Why We Sometimes Push Away the People We Love Most
• What It REALLY Means to Protect Your Peace
• Why We Misunderstand Each Other So Easily
• 12 Quotes About Listening to Yourself and Discovering What Your Heart Already Knows
• How Do You Know Whether It’s Time to Listen, Work, or Act? 

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